I sat in a boardroom, wearing a button-up shirt which is not something I do for work most days. The meeting went well; objectively, probably my best job interview ever. I was more relaxed that a typical interview because the company headhunted me, the CEO calling me directly. The told me they had a problem, and they thought I was the guy to help them solve it.
Better salary. Better benefits. Better hours. Immediate equity in a profitable, well-established business.
Everything you’d want out of a career, right?
Let me be honest about something. I wasn’t there because I only wanted the job. I wanted the feeling it gave me — the “see, you still matter” boost of extrinsically motivated self-confidence. It’s that kind of high most of us get when someone outside your world sees your value.
I’m a sucker for external validation. It’s something I’ve known about myself for a pretty long time. Sitting in that boardroom, it felt less like a character flaw and more like a life raft.
I finished the interview and had their formal offer in my inbox before I made it to my car. In reality, I could have signed it that afternoon and walked away from the company I co-founded, stepping into something new where I was admired.
Instead of signing the offer right then, I started driving, and somewhere between the boardroom and my office at the current job, a slow, sick anxiety started taking over.
How would I tell my boss?
How would he take it?
What would it mean to walk away from something I helped build — something I still believe in, even if the excitement is gone?
I got to the office and sat down across from my boss. We’ve been friends for a long time — longer than we’ve worked together — so I tried to speak as plainly as I could. But all I could manage was:
“I’m a total wreck.”
And then I broke.
It was one of those moments where my shoulders shook, my face was in my hands, and I was crying the kind of tears that make conversation impossible. It was stress, a strange kind of regret, and a grief I couldn’t have seen coming.
That was several months ago, and I’ve thought about that experience over and over again. I still don’t really understand why it hit the way it did. I don’t think there was a single reason. I didn’t hate my job. I wasn’t out of options. And I wasn’t even sure I wanted the new one.
There was one thing the emotional fallout made painfully clear: Trying to be exceptional had worn me down.
For years, I’d been trying to hold it all together. I’d worked so many long hours, away from home, and often in harsh weather conditions. The job of building systems for the company turned into the job of filling out volumes of paperwork. I made spreadsheets in the passenger seat of my truck and wrote training doc from hotel rooms. I told myself and my family that this was the price of building something. I repeated to myself over and over the lie that if I just kept pushing, eventually I would arrive at a role I loved, the balance I desperately needed, and a version of myself that felt like less of a contradiction.
But it never came; still hasn’t.
I helped build the company because what it’s doing is awesome, but I came to build systems. Instead, I ended up in the field, troubleshooting jobs, grinding through endless to-do lists of thankless tasks, and trying to convince myself (sometimes hourly) that if I could just be excellent enough at everything then maybe the work would start to love me back.
It never did. At least not in the way I needed.
If you’ve been following the series so far, this is the part where I wish I could say I learned something profound. That my boardroom conversation or the weeping incident in my boss’s office helped me discover my true calling or finally reclaim some sense of purpose, but it didn’t Not yet anyway.
But, there was one, valuable realization: exceptionalism — this need to prove myself, to be the guy who always comes through, the one who gets invited to the next big thing — was quietly wrecking me.
Like most things in life, it wasn’t dramatic. It was slow. Almost invisible. Being the fixer — the doer, the one who shows up — sometimes felt satisfying. But more often, it just felt, I don’t know. Tired, maybe. And if I’m honest, there were moments (more than a few) when it slipped into resentment. I kept asking myself: why am I sacrificing so much to build something for someone who may never really see what it costs me?
I realize now that I was chasing someone else’s version of “better.” And it was costing me the kind of life I actually want to live.
It’s weird how long it takes to notice something’s broken when it’s technically still working. The company was doing fine; great actually. I was doing fine. But it wasn’t really mine anymore — not in the way I wanted it to be. The version of “me” who’d started it had drifted away, one day in the field at a time, until all that was left was someone playing a role I didn’t know anymore.
It was another one of those “sit in the car for too long moments.” It was crying in my boss’s office.
I turned down the shiny new offer and walked right back into the mess I hadn’t sorted out yet.
Here’s what’s different now (most days anyway): I’m not trying to be exceptional anymore. I’m trying to be more honest.
For me, trying to be more honest with and true to myself shows up in weird ways. It shows up when I take the slower client call instead of the urgent but less important one. I’m trying to say not to more projects that sound cool but feel empty.
This is the most important one: when I remind myself that my wife and kids never once asked me to be a rock star — just to be with them.
I still chase approval, but I want to give up the chase. I don’t want to burn out trying to impress people who will forget what I built as soon as they hire someone new. I want to show up more consistently for my actual life. The small, quiet, often unremarkable, un-sparkly one, but the one that feels real in my bones.
Speaking of honesty, there are still days when I wonder if I made the wrong call. I’m still faced with days when the clarity fades and I miss the momentary high I felt of being wanted. But I’m watching that more closely now. I’m paying attention to where I’m looking for external validation and where it’s actually feeding that validation; fueling a version of myself I don’t want to maintain anymore.
In the meantime, I’m doing the unremarkable work of building something perhaps a bit quieter.
Something true to who I want to be.
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